By Michelle Slade
“Throwing a wing and foil board off the back of the boat, jumping into shimmering, warm, turquoise water and catching a nice trade breeze on my wing was a very cool experience while I was in the Caribbean this past winter,” says Jamie Deardorff, an avid sailor and sports person from Santa Barbara, California. “There are so many awesome spots in the Caribbean where you can go shred on a wing, where it is quiet, always pretty, and with a nice steady breeze, whether it be off a boat at anchor in a harbor or off a stunning beach. It’s the best.”
Deardorff spent several months last winter cruising and racing on a friend’s catamaran in St. Maarten and Guadeloupe. He spent a lot of time on his wingfoiling gear because conditions were consistently perfect — and easy — one of the reasons for wingfoiling’s growing popularity.



But wingfoiling is considered an easier sport. Kiteboarding utilizes long lines and requires careful attention when launching and landing. In wingfoiling, the rider doesn’t go as fast, there is no risk of tangling lines because the “wing” is hand-held, and the gear is just more maneuverable. The sport even has its own vernacular, like, “lift off” (getting up on foil), “splash down” (coming off foil), and “taxi-ing” (standing on the board and cruising along but not on foil). The learning curve is quick if one has previous experience riding a foil; if not, be prepared to put time in on the water, or better still, take a few lessons on an electric foiling board to get the feel of the foil.
The most coveted condition for wingfoiling is a wide-open sandy beach with a steady side-to-onshore breeze, so it is not surprising that many Caribbean islands offer opportunities for experienced (and newbie) wingers. Tommy Gaunt runs a water sports operation at Anegada Beach Club in the British Virgin Islands and has expanded the center to offer wingfoiling on the south side of the island where the water is deep enough to launch a wingfoil board — the hydrofoil that is attached to the bottom of the board needs water depth.
“We have a lot of visitors to the island interested in wingfoiling thanks to the great conditions for learning — calm, flat water and steady breeze,” says Gaunt. “We use the south side of the island for taking beginners out on our boat so that we can follow them around, which facilitates their progress in getting up on the foil. We take them downwind first, then get out and hit the wind line and hopefully the beginner is able to get up. The most challenging part for students is learning how to foil, which is 80 percent of the sport. Most people can fly the wing in half an hour but understanding the way that the board lifts when it begins to get up on the foil takes getting used to.”
Jake Kelsick,born and raised in Antigua, owns a watersports center with a focus on kiteboarding, wingfoiling and wake foiling. He’s traveled all over the world to partake in kiting and wingfoiling, but home in Antigua is where he likes to be.
“Wingfoiling has been blowing up over the past few years, it’s been crazy to see the growth,” enthuses Kelsick. “The local Antigua scene is still tiny — maybe ten to twenty of us just like it was with kiting, but people are coming to Antigua on vacation to wingfoil and bringing their gear with them. About 40 percent of our students are taking wing lessons compared to two years ago when we had zero students taking lessons. There’s a huge interest.”
Kelsick notes that lessons are $150/an hour, give or take, with lessons lasting up to two to three hours depending on what a winger needs. All gear and boat support are provided.
“The biggest challenge is foiling, and even when you do know how to foil the next step is putting it all together, having enough time so that you have at least three days to build a foundation,” says Kelsick. “Once you get on the foil the only thing that changes is your power source and the wing is all about controlling that power source.”
Wingfoil racing events in the Caribbean are slowly evolving. In 2023, Puerto Rico hosted the North American Championship and AWBG (World Beach Games) Continental Qualifier; Antigua Sailing Week now offers a pure wingfoiling competition which Kelsick has been instrumental in organizing, and in the Dominican Republic, the annual Cabarete Wing Fest held in the summer is an extravaganza of racing, pro clinics, epic downwinders, gear demos and of course, great Caribbean beach parties and is now a fixture on that island’s calendar.
This winter, get your wingfoiling game on at any one of the Caribbean’s wingfoil hot spots:
- Martinique: Vauclin, Anse Michel, Sainte-Anne, and Cape Knight
- Dominican Republic: Cabarete, Las Terrenas, Playa Grande, Punta Cana, Puerto Plata
- Turks and Caicos: Long Bay Beach, Grace Bay, Leeward Beach, Salterra Beach, Bell Sound, Plandon Cay Cut, McCartney Cay, Middle Creek Cay, Long Cay
- Bonaire: Lac Bay
- St Lucia: Coconut Bay Beach
- Puerto Rico: Playa las Picuas, Rio Grande, Playa Ocean Park, Vivo Beach, Shack Beach
Or follow Deardorff’s foiling wake: Wing from your private or charter boat where the launch possibilities are simply unlimited.













